FAPyGN – 2,6-diamino-4-hydroxy-5-formamidopyrimidine

Name
WID	FAPyGN
Name	2,6-diamino-4-hydroxy-5-formamidopyrimidine
Traditional name	N-(2,4-diamino-6-oxo-3H-pyrimidin-5-yl)formamide
IUPAC name	N-(2,6-diamino-4-oxo-1,4-dihydropyrimidin-5-yl)formamide
Cross references	CAS: 51093-31-3, PubChem: 75523584

Classification
Type	modified_nucleobase

Structure
Empirical formula (pH 7.5)	H₇C₅N₅O₂
SMILES (pH 7.5)	NC1=C(NC=O)C(N=C(N1)N)=O
Charge (pH 7.5)	0
Is hydrophobic	False
Molecular weight (Da)	169.14
van der Waals volume (pH 7.5; Å³ molecule^‑1)	133.97
pI	11.53
logP	-2.74
logD (pH 7.5)	-2.75

Function
Reaction participant	DNA radiation (gamma-ray) induced base oxidation (guanine ==> 2,6-diamino-4-hydroxy-5-formamidopyrimidine; hydroxyl radical) gamma_radiation[e] + GN[c] + H[c] + hydroxyl_radical[c] ⇒ FAPyGN[c] base excision (2,6-diamino-4-hydroxy-5-formamidopyrimidine) [c]: FAPydGMP + H2O ⇒ DR5P + FAPyGN

Comments
Comments	78.5 lesions per 10^6 bases [PUB_0479]; recognized by endonuclease III, FPG, UNG [PUB_0473]
References	Guetens G, De Boeck G, Highley M, van Oosterom AT, de Bruijn EA. Oxidative DNA damage: biological significance and methods of analysis. Crit Rev Clin Lab Sci 39, 331-457 (2002). WholeCell: PUB_0479, PubMed: 12385502 Hatahet Z, Kow YW, Purmal AA, Cunningham RP, Wallace SS. New substrates for old enzymes. 5-Hydroxy-2'-deoxycytidine and 5-hydroxy-2'-deoxyuridine are substrates for Escherichia coli endonuclease III and formamidopyrimidine DNA N-glycosylase, while 5-hydroxy-2'-deoxyuridine is a substrate for uracil DNA N-glycosylase. J Biol Chem 269, 18814-20 (1994). WholeCell: PUB_0473, PubMed: 8034633

Metadata
Created	2012-10-01 15:06:57
Last updated	2012-10-01 15:12:09